About The Role

What if your ability to think like an attacker could directly make organizations more secure? We're looking for a Lead Penetration Tester to conduct sophisticated offensive security engagements — probing applications, networks, and cloud environments for vulnerabilities before the real adversaries do.

This is a fully remote contract role built for experienced offensive security professionals who thrive on technical challenge, think creatively under pressure, and communicate findings with clarity and precision.

What You'll Do

Plan and execute penetration tests across web applications, internal and external networks, and cloud infrastructure
Identify, validate, and exploit vulnerabilities to demonstrate real-world impact
Conduct post-exploitation analysis to assess the full scope and blast radius of discovered weaknesses
Deliver clear, structured technical reports with actionable severity assessments and remediation guidance
Challenge and validate defensive assumptions — test detection logic, not just defenses
Support recurring red-team and purple-team engagements alongside security operations teams

Must-Have

Who You Are

Proven background in offensive security, penetration testing, or red teaming
Hands-on experience with common exploitation frameworks, tools, and methodologies (Metasploit, Burp Suite, Cobalt Strike, or similar)
Strong ability to think like an adversary and replicate real-world attack chains
Skilled at writing structured, professional technical reports that non-technical stakeholders can act on
Self-directed and reliable — you can manage engagements independently without hand-holding

Nice To Have

Offensive security certifications (OSCP, OSWE, OSEP, CRTO, or similar)
Experience with cloud-specific attack paths (AWS, Azure, GCP)
Background in red team operations, adversary simulation, or threat emulation
Familiarity with purple team collaboration and detection engineering workflows

Why Join Us

Fully remote — work from wherever you do your best work
Freelance autonomy with consistent, substantive engagements
Work on technically challenging targets across diverse environments
Contribute findings that directly improve real-world security posture
Potential for ongoing contract work and expanded engagements over time

Job description